Manufacture of aromatic derivatives of formamid



Patented Oct 7, 1930 4 UNITED STATES" PAT Y iRUDoLF WIE'IZEL,F'LUDWIGSI-IAFEN-ON-THE-RHINE, GERMANY, ASSIGNOR 'ro I. G.rannnnmnus'rnm AKTIENGESELLSGHAFT, or, rnANKroR'r-oN-MAIN, GERMANY,

A CORPORATION OF GERMANY MANUFACTURE or AnoMA'rrc DERIVATIVES or F RMAMD No Drawing. Application filed March 11', 1926, seim no. 94,042, and inGerman March 13, 1925.1

. I have found that aryl derivatives of form amid are produced by theaction of carbon monoXide at an elevated pressure on aromatic amines,which term comprises primary and Carbon mon-" secondary aromatic amines.oXid reacts with aromatic amines at room temperaturebut the reaction isconsiderably accelerated byraising the temperature for example to from70 to 100C. or more and by tions ofthe reaction will produce the formylradical, together with those containing the formyl group will bereferred to in the following and in the claims as a formic acid body t ai For example 100 parts, by weight, of aniline are filled into anautoclave capable of resist ing high pressure, with an addition of 5parts it of methyl alcohol and 1 part of metallic so dium, and theatmosphere contained in the autoclave is replaced by gaseous ammonia.The vmixture is then heated to from.180to 200 C. and carbon monoxid or agas rich in carbon monoxid is forced in under a pressure of 200atmospheres. After maintaining the temperature for a few hours anilineis converted into formanilide and the product is worked up in a suitablemanner. Instead of sodium and methyl alcohol a small amount of causticsoda or a concentrated solution thereof or metallic i sodium orpotassium alone may be used as catalysts. When working without anaddition of catalysts, I prefer to add to the aniline an amount offormanilide.

The conversion of other aromatic amines for example mono-ethyl anilineinto the corresponding formamid for example ethyl formanilide can beeffected in a similar manner. 7

Instead ofcarbon monoxid, gases containemploying catalysts. Verysuitable catalysts on an aromatic amine containing at least one hydrogenatom attached to the amino nitrogen, with carbon monoxide undersuperatmospheric pressure. a

2. A. process of manufacturing an aryl substituted formamide whichcomprises acting on an aromatic amine containing at. least one hydrogenatom attached to the amino nitro gen, with'carbon monoxide atatemperature of at least 0. and under superatmospheric pressure.

8. A process of manufacturing an aryl sub stitute d formamide whichcomprises acting f on an aromatic amine containing at least one hydrogenatom attached to the amino nitrogen,with carbon monoxide undersuperatmosmy hand. i

\ r RUDOLF WIETZEL;

ing it such as blue gas may be used, and such gases are preferablypassed through the liquid 50 reaction mass and the waste gases arecooled

